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Separatory determination of diastereomeric ibuprofen glucuronides in human urine by liquid chromatography/electrospray ionization‐mass spectrometry
Author(s) -
Ikegawa Shigeo,
Murao Naoaki,
Oohashi Junji,
Goto Junichi
Publication year - 1998
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/(sici)1099-0801(199811/12)12:6<317::aid-bmc752>3.0.co;2-t
Subject(s) - chemistry , diastereomer , chromatography , electrospray ionization , mass spectrometry , glucuronidation , electrospray , glucuronide , ammonium acetate , enantiomer , high performance liquid chromatography , urine , organic chemistry , biochemistry , enzyme , microsome
A method for the separatory determination of diastereomeric isomers of glucuronic acid conjugates of ibuprofen having a carboxyl group at the chiral center by liquid chromatography (LC)/electrospray ionization (ESI)‐mass spectrometry (MS) has been developed. The authentic specimens of acyl glucuronides of R (−)‐ and S (+)‐ibuprofen were chemically synthesized by the Mitsunobu reaction. In the ESI mode, the glucuronides were characterized by an abundant quasi‐molecular ion [M − H] − , and the formation of the negative ion was markedly influenced by a drift voltage. The resolution of diastereomeric isomers was achieved on a Develosil ODS‐HG‐5 column with 20 m M ammonium acetate (pH 5.0):acetonitrile (5:2, v/v) as a mobile phase where diastereomers were monitored with a corresponding quasi‐molecular ion. After oral administration of racemic ibuprofen, a preferential excretion of ( S )‐ibuprofen glucuronide into the urine was observed. Copyright © 1998 John Wiley & Sons, Ltd.